Sanderson et al., U.S. Pat. No. 4,910,349, disclose the preparation of t-butyl alcohol by the catalytic decomposition of t-butyl hydroperoxide (TBHP), preferably solution in t-butyl alcohol, in the presence of a metal phthalocyanine of a metal of Group IB, Group VIIB or Group VIIIB, for example chloroferric phthalocyanine and rhenium heptoxide-p-dioxane or oxotrichloro-bis-(triphenylphosphine) rhenium V. Various ratios of Fe to Re and Fe +Re to TBHP were studied.
Sanderson et al., U.S. Pat. No. 4,922,034, disclose decomposition of t-butyl hydroperoxide to t-butyl alcohol using a metal porphine catalyst, for example tetraphenylporphine, optionally promoted with a thiol and a heterocyclic amine.
Sanderson et al., U.S. Pat. No. 4,912,266, disclose decomposition of t-butyl hydroperoxide with an imidazole-promoted metal PCY catalyst, for example Fe(Ill)PCYCl or Mn (Il) PCY or VOPCY.
Marquis et al., U.S. Pat. No. 4,992,602, disclose a continuous method for converting isobutane to isobutyl alcohol including the step of decomposing t-butyl hydroperoxide to t-butyl alcohol, using a monocyclic aromatic solvent and a PCY decomposition catalyst.
Derwent abstract (Week 8912, Other Aliphatics, page 58) of reference 89-087492/12 (EP 308-101-A) discloses decomposition of t-butyl hydroperoxide to t-butyl alcohol using a metal porphine catalyst such as a trivalent Mn or Fe tetraphenylporphine, optionally promoted with an amine or thiol, or a soluble Ru catalyst promoted with a bidentate ligand such as Ru(acac)3 promoted with bis(salicylidene)-ethylenediamine, or a promoted PCY catalyst such as a Mn, Fe or vanadyl PCY promoted with an amine, a Re compound such as NH.sub.4 ReO.sub.4, a mercaptan and a free radical inhibitor, a base or a metal borate.
Lyons et al., U.S. Pat. No. 5,120,886, issued Jun. 9, 1992, which is incorporated by reference herein, teaches decomposition of hydroperoxides with metal ligand complexes in which hydrogen in the ligand molecule has been substituted with electron-withdrawing elements or groups, for example halogen or nitro or cyano groups.
Related catalysts to those used according to the invention have been previously disclosed for use in oxidizing alkanes to the corresponding alcohols. For example, perhalogenated metal complexes have been disclosed in Ellis et al., copending application Ser. No. 07/568,116, filed Aug. 16, 1990, the disclosure of which is herein incorporated by reference. Other patents disclosing use of metal coordination complex catalysts in oxidation of alkanes are Ellis et al U.S. Pat. Nos. 4,895,680; 4,895,682 and 4,970,348.